Whipping Filly by Anon 
(Caretaker / Filly)
wip

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>Count Knightly had a daughter.
>Said daughter, Lily has recently reached the age of five and her behavior suggested a need for a spanking.
>As such, he needed a suitable pony to be spanked in her stead. Physical punishments were a big no-no for a filly of his daughter’s stature after all.

>Lily’s first punishment of this nature began when she was caught sneaking around in places within the castle which were off limits to her.
>Her parents had already brought her to her room and were awaiting their best guard to bring them their newest castle staff member.
>The guard soon returned with a filly the same age as Lily, this was Blossom.
>Blossom looked very similar to Lily, she sported the same colors and even had a similar stature and voice. The only difference was the tone of the colors and some stripes.
>Count Knightly took great care to employ a pony who looked like her daughter as much as possible. he believed a close resemblance might have a bigger effect on Lily during punishments. This particular pony was took quite the effort to hire, but the count believed it was more than worth it.
>”I hast brought the whipping filly as ordered.”
>”Good.” Said Countess Grape. “We may begin the punishment.”
>”B-but, already?!” Said Blossom, who had just got here earlier that day. She had been rather nervous about her new job as one would expect and didn’t expect her young mistress to get into trouble already.
>”Of course! Mine little lily won’t learn her lesson by herself, after all.” The countess took a seat on an armless chair. “Now, let us begin.”
>Poor Blossom didn’t know what to do. Being only five herself this was to be her first spanking ever and this left her naturally terrified. She was told that everything would be sorted out when the time came so she just stood there, not sure what to do.
>The guard suddenly picked her up with his magic and deposited her on Countess Grape’s lap. It was tradition for a guard or two to place the whipping colt or filly in the required position and hold him or her down if needed.
>This particular case was unusual in that the countess herself was going to be holding her down and delivering the spanking personally. It was rare, as the task was generally relegated to guards and servants, however the Grape insisted on handling this personally.

>The countess patted the scared, sobbing filly’s bottom. “Make sure Lily’s watching the whole thing, Knightly dear.”
>”Of course, mine love!” Said Knightly as he put his hooves on his daughter’s shoulders. “Tis the most important part, after all!”
>Grape stopped patting Blossom’s bottom and raised her hoof high, and brought it down. Blossom gasped and leaned forward as much as she was able.
>The countess did not stop and showered the whipping filly’s flank with hits from her hoof. They weren’t particularly hard, but Blossom’s young age and the fact that this was her first time got her kicking, squirming, squealing and begging.
>Grape ignored these mid-spanking antics and Knightly was actually rather glad for them. Spectacle was important to drive the lesson home, after all. He was also impressed by his wife. She was spanking his employee hard enough to elicit a proper reaction but light enough for a quick recovery afterwards. Blossom was perhaps the perfect whipping filly for Lily. He was going to have to put in a lot of effort to keep her.
>Lily, for her part was forced to watch the whole thing. She had not known what a spanking was before this. Surprisingly enough, watching this filly get punished for her made her feel very guilty. She couldn’t help but reach back with a hoof as she watched her mother’s hoof at work.
>The spanking kept going, perhaps a bit longer than necessary, but Countess Grape wanted to drive the lesson home to her daughter. She would pay Blossom an extra bit for this anyway.
>Weather or not the extra bit was worth it wasn’t up to Blossom as her thrashing body was held down and her cries ignored by all but Lily, who was actually hoping this would end.
>Thankfully, it did end. Grape let the filly sob on her lap as she and Knightly scolded their daughter on the importance of playing in safe places.
>” I’ll grant the whipping filly her payment, shall thou keep with lily?” Said the countess as she put Blossom down.
>”Of course.”
>And with that, Countess Grape Escorted Blossom out of the room.
>The count gave her daughter one more short lecture. He told her that the only reason she wasn’t the one suffering over her mother’s knee was due to the whipping filly and if she didn’t want her to suffer, she would have to behave herself.
>As for Blossom, she was congratulated for a job well done by the countess and was given three bits and a bag of various candies, which was somewhat of a commodity at that time. Despite all this, she was hoping that the young mistress would not get into trouble for a long while.